Bill Cowley has often been called the “Wayne Gretzky of his day” in reference to his abilities as a playmaker. Cowley would lead the NHL in Assists three times and win the Hart Trophy twice. More importantly, Cowley would hoist the Stanley Cup above his head twice.
While Cowley, who spent all but his rookie season in Boston, earned a lot of hardware, it is worth noting that a lot of it took place during World War II, when the NHL did not have the best compliment of players, which is why this ranking may seem a little low despite his vast accomplishments. Cowley entered the Hockey Hall of Fame in 1968.
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